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Exploring the formation pathways of donor-acceptor catenanes in aqueous dynamic combinatorial libraries


Reference:

Cougnon, F. B. L., Au-Yeung, H. Y., Pantos, G. D. and Sanders, J. K. M., 2011. Exploring the formation pathways of donor-acceptor catenanes in aqueous dynamic combinatorial libraries. Journal of the American Chemical Society, 133 (9), pp. 3198-3207.

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Official URL:

http://dx.doi.org/10.1021/ja111407m

Abstract

The discovery through dynamic combinatorial chemistry (DCC) of a new generation of donor-acceptor [2]catenanes highlights the power of DCC to access unprecedented structures. While conventional thinking has limited the scope of donor-acceptor catenanes to strictly alternating stacks of donor (D) and acceptor (A) aromatic units, DCC is demonstrated in this paper to give access to unusual DAAD, DADD, and ADAA stacks. Each of these catenanes has specific structural requirements, allowing control of their formation. On the basis of these results, and on the observation that the catenanes represent kinetic bottlenecks in the reaction pathway, we propose a mechanism that explains and predicts the structures formed. Furthermore, the spontaneous assembly of catenanes in aqueous dynamic systems gives a fundamental insight into the role played by hydrophobic effect and donor-acceptor interactions when building such complex architectures.

Details

Item Type Articles
CreatorsCougnon, F. B. L., Au-Yeung, H. Y., Pantos, G. D. and Sanders, J. K. M.
DOI10.1021/ja111407m
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code23201

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